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Greatest Hits Oldies But Goodies Ever

Before the world knew him as Conway Twitty, teenage center fielder Harold Lloyd Jenkins had a contract offer waiting from Major League Baseball’s Philadelphia Phillies. Growing up in Helena, Arkansas in the early 1950s, Harold learned the game from his father, Floyd Jenkins, a Mississippi River ferryboat captain who threw baseballs with him after long shifts on the water. Though he formed the Phillips County Ramblers at age ten and played Saturday mornings on local radio station KFFA, Harold viewed the guitar only as a pastime. With fast base-running and a powerful left-handed swing in Mississippi Delta school and semi-pro leagues, he saw baseball as his lifelong career and his family’s way out of hard river-town labor. After his standout semi-pro run following high school, Phillies scouts offered him a professional contract. Before he could sign the papers, a United States Army draft notice arrived during the Korean War era. Without seeking a delay, Harold put national duty first, packed away his baseball glove, and shipped out to the Far East, serving mainly in Japan from around 1954 to 1956. Missing Arkansas and the diamond on long nights abroad, the young soldier turned to his guitar and formed a band called the Cimarrons to play military clubs, seeing firsthand how his singing comforted fellow troops. Two years in uniform cost him his peak athletic window, and when he returned home in 1956, his chance with the Phillies had passed. Hearing Elvis Presley’s debut recordings right after his discharge steered him permanently into music as Conway Twitty, launching a career that produced forty number-one singles on Billboard’s country chart. Decades later as a Nashville star with tens of millions of records sold, Twitty bought an ownership stake in the minor-league Nashville Sounds, returning to the ballpark dream he had set aside when that Army draft letter arrived before he could sign.

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BEFORE FORTY COUNTRY NUMBER-ONE HITS MADE HIM CONWAY TWITTY, HAROLD LLOYD JENKINS HAD A PHILADELPHIA PHILLIES BASEBALL CONTRACT WAITING FOR HIS SIGNATURE.

Born in Friars Point, Mississippi, on September 1, 1933, Harold Lloyd Jenkins moved across the Mississippi River to Helena, Arkansas, when he was ten years old. His father, Floyd Jenkins, worked long shifts piloting a river ferryboat, yet still came home to throw baseballs with his son and teach him the fundamentals of the game.

Music entered the house early as well. At ten, Harold put together his first group, the Phillips County Ramblers, and soon earned a regular Saturday morning slot on local Helena radio station KFFA. Even with live broadcasts under his belt, the boy treated the acoustic guitar as a weekend pastime rather than a living.

On dirt diamonds across the Mississippi Delta, baseball looked like his real future and a steady path beyond river-town labor. Blessed with quick speed on the basepaths and a strong swing in high school and semi-pro leagues, Harold drew serious attention from Major League scouts.

Following a standout semi-pro stretch after graduation, the Philadelphia Phillies offered him a professional contract. Before he could put pen to paper and report to the organization, a draft notice arrived from the United States Army during the Korean War era.

Rather than seeking a deferment, Harold packed away his glove, answered the call, and shipped out to the Far East from 1954 to 1956. Stationed in Japan thousands of miles from Arkansas ballfields, the young soldier leaned on his guitar to pass the long evenings abroad.

While in uniform, he organized a country band called the Cimarrons—also billed on base circuits as the Fuji Mountain Boys—to entertain fellow American troops in military service clubs across Japan. Playing night after night for homesick soldiers showed him for the first time how completely his voice could hold a room.

When Harold returned stateside in 1956, the Phillies actually renewed their interest in signing him, even after two years away from competitive ball. By then, however, he had heard Elvis Presley’s early Sun Records releases coming out of nearby Memphis, and the pull of a microphone finally overtook the outfield.

In 1957, looking at a road map for a stage name that would stand out, he paired Conway, Arkansas, with Twitty, Texas. After breaking through in rock and roll with the 1958 million-seller “It’s Only Make Believe,” Conway Twitty walked away from pop clubs in 1965 to sing traditional country music full-time.

Over the next quarter century, that pivot produced forty number-one singles on Billboard’s country chart, from “Next in Line” and “Hello Darlin'” to his celebrated duets alongside Loretta Lynn. Still, tens of millions of records sold never took the ballpark out of him.

In the late 1970s, after drummer Jimmy “Snuffy” Miller introduced him to Vanderbilt baseball coach Larry Schmittou’s plan to bring professional baseball back to Music City, Twitty stepped up as a lead investor to help finance Herschel Greer Stadium and launch the Double-A Nashville Sounds for their inaugural 1978 season. Taking a twenty-percent stake, he recruited fellow country singers Jerry Reed, Cal Smith, and Larry Gatlin, along with the Oak Ridge Boys’ Richard Sterban, into the ownership group.

Even while crisscrossing North America on his tour bus, Twitty regularly telephoned team general manager Farrell Owens from the road just to ask for that night’s score.

More than twenty years after an Army draft letter kept Harold Jenkins from signing his first pro contract, Conway Twitty still found his way into a ballpark dugout—calling in after showtime to check on his team.

https://www.youtube.com/watch?v=_LpnL-RLJrc

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In May 2025, Alan Jackson ended over thirty years of highway touring so he could enjoy his young grandsons while still walking on his own feet. Throughout the height of his country career, Jackson spent nearly every weekend on tour buses playing arenas and fairgrounds nationwide. Those dates built a long run of number-one records, even as constant travel kept him away from home for countless Saturdays while he and his wife, Denise, raised their three daughters. Priorities shifted once a third generation entered the family. Welcoming grandsons Jackson Bradshaw in late 2022 and Wesley in 2024 gave the sixty-six-year-old singer a clear reason to wind down his schedule as he mapped out the 2024 and 2025 final leg of his Last Call tour. Living with Charcot-Marie-Tooth disease brought real urgency to that timeline. Diagnosed in 2011, the inherited nerve disorder has no cure and steadily wears down balance and lower-leg sensation. Staying on the road a few years longer meant risking the window when he could still walk steadily and keep up with the boys around the house. Rather than holding onto sold-out arenas until physical decline made the decision for him, Jackson left the tour circuit early enough to trade hotel rooms and overnight bus rides for unhurried days beside Denise and their daughters. Decades of concert bookings had once pulled a young father down the interstate nearly every weekend. Parking the buses in 2025 gave Alan Jackson those weekends back at home, while he still has the footing to share them with his grandsons.

After guarding her heart alone for 23 years, Grand Ole Opry star Skeeter Davis married a long-haired rock bassist 17 years her junior at age 56 in 1987. Loss had trailed her for decades. After surviving the 1953 car crash that killed her singing partner Betty Jack Davis, Skeeter endured two painful divorces. Her early marriage to Kenneth DePew ended in betrayal, and her four-year union with Nashville broadcaster Ralph Emery collapsed in 1964 amid tight control, distrust, and lost pregnancies. Convinced happiness with a man was out of reach, she lived quietly on her Brentwood, Tennessee farm with her pets. Everything shifted when the devout Christian country traditionalist met Joey Spampinato, bassist and songwriter for the Northeastern rock band NRBQ. Their studio chemistry produced the acclaimed 1985 collaborative album She Sings, They Play. Joey also wrote gentle music specifically for her voice, restoring the simple joy of singing after years of industry fatigue. Conservative Nashville circles doubted a marriage between an Opry veteran and a 39-year-old rocker would last. Instead, their real test arrived in 1988, just a year after the wedding, when Skeeter was first diagnosed with breast cancer. Joey stayed firmly beside her through surgery and exhausting treatment. Road life and personal circumstances eventually led them to divorce in 1996 after nine years together, without the bitterness of her past marriages. Until she passed away in 2004, Skeeter spoke of those years with Joey as the season of her life when she felt most loved and free to be herself.

On his fourth studio album, 2005’s Time Well Wasted, Brad Paisley co-wrote and recorded the ballad She’s Everything as a personal gift for his wife, actress Kimberly Williams-Paisley. Married in 2003, the couple navigated public careers split between country music arenas and Hollywood film sets. Away from red carpets and formal gowns, Kimberly kept a modest daily routine that brought calm honesty into an industry built on spectacle. She kept driving her older Saturn with its open sunroof and felt most at ease at home in worn running shoes and torn jeans. Paisley quietly took note of all of it. Passing over conventional romantic clichés, he built the ballad out of those small, familiar details from their life together. Alongside that playful, easygoing side, the song honored the spiritual steadiness she brought into their marriage. Whenever tour buses, packed schedules, and the pressures of fame pulled him away, Kimberly remained his calm refuge at home, bowing her head in prayer beside him through uncertain seasons. To close the portrait, Paisley looked decades ahead toward old age, ending with a simple wish that the two of them would pass through the years and sit side by side in a rocking chair at ninety. Listeners embraced the ballad because its affection lived in unguarded, everyday moments. Over twenty years into their marriage, the love Paisley captured in 2005 still comes down to scuffed running shoes, a modest car, quiet faith, and that rocking chair waiting down the road.

When Loretta Lynn walked into Patsy Cline’s Nashville home in 1961 wearing homemade clothes, country music’s biggest female star opened her bedroom closet and handed over her own stage wardrobe. Their bond began that summer after a serious car crash nearly ended Patsy’s life. When Loretta, fresh off her first chart entry, sang one of Patsy’s songs for her on Ernest Tubb’s Midnight Jamboree, Patsy heard it from her hospital bed and sent her husband, Charlie Dick, to bring her in. Loretta was a shy mother of four from Butcher Hollow, Kentucky, sewing clothes on an old machine after sleeping in cars with her husband, Doolittle Lynn, to promote her record at small radio stations. With the Grand Ole Opry ahead, Patsy piled expensive gowns, fur coats, shoes, and jewelry into Loretta’s arms, telling her petite friend to take the waists in and walk onstage proud. Male-dominated Music Row gave women scarce room on early 1960s radio and tours. Instead of seeing a rival, Patsy became Loretta’s shield. She taught her to stand tall onstage, negotiate fair pay with promoters, order confidently in restaurants, and hold her ground with a hot-tempered husband. On the night of March 3, 1963, in Kansas City, Patsy slipped delicate silk underwear into Loretta’s purse as a gift, knowing her frugal friend never bought luxuries for herself. Two days later, Patsy died in a plane crash near Camden, Tennessee, at age 30. Loretta kept those dresses for decades and stored that silk gift unwashed in a drawer so no trace of Patsy would fade. Their friendship lasted less than two years. Over the next half century, Loretta said she never would have had the courage to stay in Nashville without Patsy’s open closet, and she spent her career guiding the women who followed.

During his final road show in Milwaukee on May 17, 2025, Alan Jackson settled onto a simple stool onstage to sing Where Were You (When the World Stopped Turning). For over three decades on tour, the six-foot-four Georgia singer had stood steady at the center microphone. By that sold-out Saturday night at Fiserv Forum, progressive nerve damage from Charcot-Marie-Tooth disease had worn down balance and sensation in his legs, leaving him seated calmly under the stage lights. Nearly twenty-four years earlier, that ballad had arrived in quiet solitude. For weeks after September 11, 2001, Jackson struggled to write about the attacks because he wanted neither a vengeful song nor anything that felt like capitalizing on tragedy. Around four in the morning on Sunday, October 28, 2001, he woke with the melody and chorus in his mind, sang them into a handheld recorder, and finished the verses later that morning while his family attended Sunday school. Rather than leaning on anger or politics, the song pointed listeners back toward faith, hope, and family closeness. After debuting it from a stool at the November 2001 CMA Awards, Jackson assumed the moment would eventually fade from his shows, only to see audiences years later still waiting in the dark to hear it. Inside the darkened Wisconsin arena, thousands of fans lifted glowing cell phones until the tiers of Fiserv Forum shone around him. Across the hushed bowl, older listeners and veterans wiped their eyes, remembering autumn 2001 as the voice who carried them through it prepared to leave the highway. A song written alone before dawn in 2001 had once offered millions of grieving Americans steady ground. Twenty-four years later, surrounded by raised lights in Milwaukee, those same quiet chords held Alan Jackson up on his final night of the road.

In February 2001, Little Jimmy Dickens welcomed Brad Paisley into the Grand Ole Opry, starting a friendship across 52 years that gave the Opry veteran a lively new chapter. Dickens was nearly 80 and the Opry’s oldest living member when he first greeted Paisley there in 1999, two years before standing on the wooden circle to induct the 28-year-old singer. Four feet eleven in bright rhinestone suits beside the tall guitarist in a white cowboy hat, Dickens found an easy partner backstage, where Paisley skipped stiff deference and joked with him as an equal, keeping their dressing rooms full of laughter. Refusing to let older stars fade behind modern country radio, Paisley cast Dickens in hit music videos including “I’m Gonna Miss Her,” “Celebrity,” “Alcohol,” and “Online.” They also recorded album comedy skits and appeared together at the CMA Awards, introducing Dickens’s grin and wit to millions of young viewers in the 2000s and keeping his eighties and nineties busy. On Christmas Day 2014, Dickens suffered a stroke at age 94. Paisley visited his Nashville hospital room often to sit with Dickens’s wife, Mona, bringing his guitar to play familiar melodies beside the bed. Even when Dickens grew weak and could barely speak, his breathing and face eased whenever Paisley played, before he passed away on January 2, 2015. On January 8, his flower-covered casket rested beside the oak circle on the Grand Ole Opry House stage. Delivering a eulogy where they had performed together so many nights, Paisley paused to hold back tears over the empty Opry dressing room, then picked up his guitar to play a traditional hymn. Paisley still carries that example forward today, welcoming younger artists into the Opry the same way a friend in a rhinestone suit once welcomed him onto the circle.

During his final road show in Milwaukee on May 17, 2025, 66-year-old Alan Jackson sang Drive (For Daddy Gene), the tribute he wrote for his late father, Eugene. Raised in Newnan, Georgia, in a modest home built around his grandfather’s old toolshed, Jackson grew up watching Joseph Eugene Jackson work quietly with his hands. After his father died on January 31, 2000, Jackson tried several times to write about him, setting aside sad ballads until he found a way to capture the everyday memories they actually shared. Released in January 2002, the song went to number one by recalling how father and son fixed up an old pickup truck and took a small boat out on the lake, traditions Jackson later shared with his three daughters. Inside Milwaukee’s Fiserv Forum, family footage projected behind the stage brought those rural Georgia years before 17,000 fans on the closing stop of his Last Call: One More for the Road Tour. Singing that tribute on his final night of road touring carried an unmistakable weight. Along with his steady Southern work ethic, Eugene Jackson had unknowingly passed down Charcot-Marie-Tooth disease. Publicly shared by Alan in 2021 after a decade with the diagnosis, the progressive nerve disorder gradually weakened his legs and balance until more than thirty years of highway touring had to end. Standing at the microphone, Jackson let none of that physical toll turn into bitterness. His delivery held only plainspoken gratitude for the quiet workingman who gave him a love for old machines and grounded his songwriting in ordinary Southern life.Decades after those childhood lessons on back roads and lake water, the tour buses were finally parking for good. Before leaving the highway behind, Alan Jackson gave one of his last road performances back to the man who first trusted him behind the wheel.

Fame in Nashville and Hollywood nearly cost Kris Kristofferson his life before he met Pepperdine law student Lisa Meyers at a gym in Malibu. In late 1980, his second marriage to singer Rita Coolidge ended just as his costly Western, Heaven’s Gate, failed with critics and audiences. Hollywood studios walked away. Deep in depression and daily drinking, Kris was warned by a doctor that his failing liver would not last much longer. When they met in 1982, Kris was 46 and Lisa was 26. Outsiders doubted his match with a calm, private student twenty years younger. Wanting a healthy future with her and a family led him to quit hard liquor, and they married on February 18, 1983, at Pepperdine’s Stauffer Chapel. Instead of pursuing an independent law practice, Lisa worked behind the scenes to manage Kris’s career and protect his business. Stability at home revived his songwriting, and in 1985 he formed The Highwaymen with Johnny Cash, Waylon Jennings, and Willie Nelson. They raised five children together: Jesse, Jody, Johnny, Kelly Marie, and Blake. Lisa also stayed close to his three older children, Tracy, Kris Jr., and Casey, uniting all eight. In the early 1990s, they traded Hollywood and Nashville for remote Hana on Maui, where neighbors saw Kris mowing his property on a tractor. In his final decade, severe memory loss was misdiagnosed as Alzheimer’s until doctors identified chronic Lyme disease in 2016. After he retired in 2021, Lisa cared for him privately at home, guarding his dignity every day. He passed away peacefully at home on Maui on September 28, 2024, at age 88. Forty-one years after meeting in a Malibu gym, Lisa had stood beside him to the end, holding their family together far from the spotlight.

On May 17, 2025, 66-year-old Alan Jackson stepped up to the microphone before a sold-out crowd at Milwaukee’s 17,000-seat Fiserv Forum and announced his final night out on the road. The Wisconsin concert closed his Last Call: One More for the Road Tour after more than three decades of carrying traditional country music across America. Progressive nerve damage from Charcot-Marie-Tooth disease had steadily stripped away balance and sensation in his legs, turning every walk across an arena stage into a careful effort. Behind him and his longtime band, The Strayhorns, big screens showed photographs and video of his younger self while his voice filled the room. Pausing during the set to address the packed house, Jackson told fans he was winding down and confirmed that Milwaukee was his last road show. Across the arena, thousands rose at once in roaring applause and a standing ovation, prompting Jackson to admit into the microphone that they were going to make him tear up onstage. Looking out over the seats, he reflected back forty years to the September he and his wife drove into Nashville pulling an old U-Haul trailer to chase a music dream. From that modest arrival, tour buses carried his songs coast to coast countless times, leading him to call the journey a long, sweet ride and say he had lived the American dream. Although he promised one final hometown show in Nashville where his career started, that night in Milwaukee officially ended his decades of highway touring. Jackson never faded quietly out of sight or waited until his singing gave out. With a capacity Wisconsin crowd on its feet, he parked over thirty years of tour buses under bright arena lights, his voice clear and his pride intact.